Sodium Hydroxide → 3-Amino-9-ethylcarbazole

HRID 1763218

Reaction equation

HRID 1763218 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:8]([CH2:17][CH3:18])[C:9]3[C:14]([C:15]=2[CH:16]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3)([O-])=O.[OH-].[Na+]>Cl.O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[N:8]([CH2:17][CH3:18])[C:9]3[C:14]([C:15]=2[CH:16]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 665739-ethyl-3-nitro-9H-carbazole

Product 1

HCID 85883-Amino-9-ethylcarbazoleYield 82.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A solution of 10.2 g of 3-nitro-N-ethylcarbazole (42.5 mmol) and 38.4 g of stannous chloride dihydrate (170 mmol) in 100 ml of concentrated hydrochloric acid was heated for 3 hours at 92° C. The ice cooled solution was (cautiously) made basic by partial addition of a solution of 75 g sodium hydroxide in 150 ml of water. The product was filtered off and washed with the above base solution, followed by copious amounts of water, and then air dried. Vacuum drying and recrystallization from pyridine/water gave 7.4 g light-green needles (82% yield) mp b 109°-11° C.

Workup

  1. filtrationThe product was filtered off
  2. washwashed with the above base solution
  3. customair dried
  4. customVacuum drying
  5. customrecrystallization from pyridine/water

Sources & evidence

ORD record
ord-2e9d8db71f794180825067f2db8a5a8d
Source dataset
uspto-grants-1978_09
Patent number
US04111850

Linked notes

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